When his neck bent under the strain of leading the nation, President Lyndon B. Johnson told himself, “It could be worse. I could be mayor.” Managing an unwieldy city is no small task, and avoiding the temptations of mayoral corruption proves impossible for some. Considering the dubious reputations of politicians from Boss Tweed to Richard J. Daley, one may ask, who would want that responsibility? Aside from whack-jobs like Anthony Weiner, that is.

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In 1683 William Penn and Chief Tamanend, the revered leader of the Lenape tribe, created a lasting peace treaty between Native Americans and European settlers of the Pennsylvania Colony. Civic groups such as New York City’s Tammany Society (formed in 1786) honored Tamanend’s legacy. But by the mid-1860s, that organization had become Tammany Hall, run by avaricious politician William “Boss” Tweed. On top of being a Civil War profiteer, Tweed pilfered today’s equivalent of billions from city taxpayers—all under the name of good Chief Tamanend.

However ill-intentioned, Tweed was exceptionally skilled at getting his way. Today’s leaders often err on the side of ineffectuality. Take San Diego’s Dick Murphy, first elected to the mayor’s office in 2000. When wildfire licked the region, Murphy was slow to react. When a pension crisis gripped the city, he defunded the budget further. In 2004 he was reelected by a narrow margin but only after thousands of arguably legitimate votes for a rival were discounted. Murphy finally resigned in 2005, declaring, “A good leader knows when it is time to move on.” In 2013 mayoral successor Bob Filner took Murphy’s advice and quit amid multiple sexual harassment charges. You stay classy, San Diego.

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Boss Tweed
(1823–1878 | American politician)
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Mayoral Politicking

From humble beginnings in New York’s Lower East Side neighborhood, William Tweed started out as a fireman, worked at his father’s saddler trade, brawled and cheated his way to the top of the city’s political machine. Though well known as Boss, he was never elected to the mayor’s office; nevertheless, by 1869 the entire city was at his command. The real mayor, A. Oakey Hall, was a mere patsy, an elegant face for public view. Tweed never trucked with mayoral politicking—no baby kissing, no glad-handing. Rather, he stuck to rigging elections: In exchange for votes, he expedited citizenship for the masses arriving on Ellis Island, and his followers visited polling stations as many as 20 times each—the phrase “Vote early and vote often” dates from this time.

Harper’s Weekly cartoonist Thomas Nast was instrumental in exposing Tweed by illustrating the Boss’s greed and corruption. Annoyed, Tweed famously said, “Stop them damn pictures. I don’t care what the papers write about me. My constituents can’t read. But damn it, they can see the pictures.” After several arrests and trials during the 1870s (and one prison break), Tweed died in Ludlow Street Jail, just blocks from where he grew up.

Between 1865 and 1871, at the height of his power, Boss Tweed had his fat fingers in just about every municipal cookie jar. Nearly all businesses operating in New York City had to pay dues to Tweed’s Tammany Hall—some historians estimate that the “Tweed Ring” extorted up to $8 billion in today’s currency. At the same time, Tweed oversaw the construction of what became some of New York’s signature landmarks. During his reign, for example, the Brooklyn Bridge was begun and Central Park was nearly completed. Meanwhile, Manhattan’s grid of streets and sewers multiplied. And in order to placate his constituency, Tweed was liberal with charity, providing food and jobs for many in need.

Perhaps the only mayor to come close to re-creating the scope of Tweed’s underhanded network was Richard J. Daley, mayor of Chicago from 1955 until his death, in 1976. Like Tweed, Daley had near total control over a major U.S. city; in a 1971 biography, journalist Mike Royko even dubbed him Boss. Unlike Tweed, Daley was never charged with corruption. But many grafters and grifters in his massive inner circle were, and Chicago became overrun with fraud while Mayor Daley turned a blind eye.

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Richard J. Daley
(1902–1976 | American politician)
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The Windy City

The name Daley is synonymous with Chicago. Richard J. Daley was mayor of the Windy City for 21 years, and his son Richard M. held the office for another 22. During the Daley dynasty, Chicago weathered quite a few economic storms. In the 1960s and ’70s, when other Midwestern manufacturing cities were rusting away, Daley Sr. undertook massive construction projects, such as the Sears Tower. And Time magazine named Daley Jr. the fifth-greatest big-city U.S. mayor for creating a “period of impressive stability,” reducing the murder rate and improving education. No wonder many Chicagoans hold the family in Arthurian awe.

But the Daleys’ city was no Camelot. During the civil rights movement, Richard I effectively kept Chicago segregated, and Martin Luther King Jr. noted that “people from Mississippi ought to come to Chicago to learn how to hate.” When rioters filled the streets after King’s assassination, in 1968, Daley authorized the police to “shoot to kill any arsonist.” And in 2004 the Chicago Sun-Times besmirched Richard II’s reputation, revealing that his government had hired private trucks to do city work. The well-paid drivers did little besides collect bribes, and in some cases taxpayer money went directly to the Mob.

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The Windy City to
Mayoral Politicking

In 1876, when a tornado threatened to level Chicago, the Cincinnati Enquirer invoked the metropolis’s nascent nickname: the Windy City. The article reported no damage but couldn’t resist gibing a rival town, claiming the buildings “were so heavily weighed down with mortgages that no whirlwind could affect them.” The moniker came to refer not only to the icy winds blowing over the adjacent Great Lakes and tunneling between the skyscrapers but to political bombast. Over the years, Chicago has had its fair share of bloviators, windbags and eccentric orators, especially among mayors. Richard J. Daley was particularly prone to malaprops, referring to Alcoholics Anonymous as Alcoholics Unanimous and a tandem bicycle as a tantrum bicycle. Richard M. Daley apparently inherited his father’s ineloquence: He once offered to demonstrate a rifle’s effectiveness by sticking it up a reporter’s butt.

While hot air keeps Chicago mayors in office, its bitter weather ended the politicking of at least one. When the Blizzard of 1979 buried the city, Mayor Michael Bilandic was deemed completely useless. Mayoral hopeful Jane Byrne seized the opportunity, speaking at length about the state of the frozen burg. She defeated Bilandic in the next election.

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Mayoral Politicking to
Anthony Weiner
(b. 1964 | American politician)

In 2011 U.S. Representative Anthony Weiner resigned after “accidentally” tweeting lewd pictures of himself. The tabloids had a field day—the New York Post ran headlines like “Battle of the Bulge”—and Weiner’s political career seemed cooked. But in 2013 Weiner announced his run for mayor of New York. “Weiner’s Second Coming!” penned the Post gleefully. Nobody should have been surprised when Weiner became the race’s front-runner. After all, mayors have recovered from worse. Mayor Buddy Cianci of Providence, Rhode Island, who resigned in 1984 after assaulting a contractor and attempting to stub a cigarette in his eye, became mayor again in 1990. In Washington, D.C., Marion Barry was reelected in 1994 after having been arrested four years earlier for smoking crack cocaine.

Midway through Weiner’s mayoral bid, scandal found him once again—this time for having engaged in a sexting affair under the pseudonym Carlos Danger (after he’d claimed publicly to be reformed). No amount of politicking could save Weiner twice. Neither his fatuous assertions, such as “Quit isn’t the way we roll in New York City,” nor his childish rampages against the media for reporting on his indiscretions could redeem his reputation. Weiner’s campaign had officially gone limp.